210 
IOWA ACADEMY OF SCIENCE 
Theory for Na . CH 3 . CoH^ . COOCeHs .SD 3 H.C 5 H 5 N 
Found 
.Sulphur, 7.65 per cent. 7.69 per cent. 
Nitrogen, 6.73 per cent. 5.91-5.99 per cent. 
These figures cannot be called determinative. Lack of time 
prevented the determination of nitrogen by the absolute method. 
OONODUSIONS. 
The writer cannot help feeling as a result of his study in this 
field, that the matter of the actual formulae of the two acid 
chlorides is still unsettled. It is true that the ammonia deriva- 
tives seem to give positive results, but when we come to the 
anilides, we find that the so-called symmetrical anilide is pro- 
duced in equal quantity with the unsymmetrical anilide from 
the unsymmetrical acid chloride. 
In the case of the alcoholic derivatives the differences in be- 
havior are slight. The greater activity of the unsymmetrical 
acid chloride is manifest, and the formation of the sulphone 
chloride ester by it is different from the action of the symmetri- 
cal acid chloride which goes directly to the ester acid; but, as 
has been shown, the higher temperature required for the action 
of the symmetrical acid chloride on the alcohol would cause the 
hydrolysis of the ester of the sulphone chloride to give the ester 
of the sulphonic acid, just as it occurs on boiling the unsym- 
metrical acid chloride with alcohol. There is no reason to sus- 
pect that the mechanism of the reaction is different in one case 
from what is it in the other. 
When we come to the phenols, the behavior of the two bodies 
is the same, even to the formation of the colored compounds. 
This further complicates the reasoning, as we have not only, 
as in the case of the anilides, an unsymmetrical body giving a 
symmetrical compound in part, but also, in the case of the phe- 
nols, a symmetrical compound giving a presumably unsym- 
metrical body, and that too in practically the same proportions 
in which it is formed from the unsymmetrical chloride." 
The fact as shown by List and Stein^® that the reduction of 
the symmetrical acid chloride gives the sulphobenzid, (I) has its 
most direct and reasonable explanation in the formation from 
(II), which is, however, the formula given for the unsym- 
metrical chloride. 
^mer., 31, 164-8, 1898. 
